1,2-Dimethoxyethane → N-[6-(5-chloro-2-thienyl)-1,3-benzothiazol-2-yl]-N'-ethylurea

HRID 9165Notes

Reaction equation

HRID 9165 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.COCCOC.[Cl:23][C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:24]1[S:28][C:27]([C:2]2[CH:16]=[CH:15][C:5]3[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=3[CH:3]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343245-Chlorothiophene-2-boronic acidHCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 21985583N-[6-(5-chloro-2-thienyl)-1,3-benzothiazol-2-yl]-N'-ethylureaYield 16%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A 40 ml pressure tube was charged with about 100 mg N-(6-bromo-1,3-benzothiazol-2-yl)-N′-ethylurea, and about 2 ml ethylene glycol dimethyl ether. The slurry was stirred via magnetic stirbar followed by evacuation then release to nitrogen atmosphere (3 times). Next about 6 mol percent Pd(PPh3)4 was added, followed by about 1.1 eq of 5-chlorothiophene-2-boronic acid. Following addition of about 3 equivalents sodium carbonate in about 0.5 ml water, the suspension was evacuated and released to nitrogen atmosphere 3 times. The pressure tube was then sealed tightly and heated to about 85–90° C. for about 12–20 hours. The reaction was cooled to room temperature then purified by preparative HPLC to yield 16% of N-[6-(5-chloro-2-thienyl)-1,3-benzothiazol-2-yl]-N′-ethylurea. 1H NMR 1.1 (t, 3H), 3.2 (m, 2H), 6.75 (m, 1H), 7.18 (d, 1H), 7.38 (m, 1H), 7.6 (m, 2H), 8.19 (d, 1H), 10.75 (br s, 1H); LC/MS 3.86 min, 338 (M+1), 336 (M−1).

Workup

  1. customthe suspension was evacuated
  2. customThe pressure tube was then sealed tightly
  3. temperatureheated to about 85–90° C. for about 12–20 hours
  4. customthen purified by preparative HPLC

Sources & evidence

ORD record
ord-c6be5838f30f427eb3af2ee3a70a8206
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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